Where jazz is concerned, I'm mostly into the 50s era stuff leading up to the "new thing" aka free jazz, and then a good bit of the free jazz stuff as well. I'd recommend checking out Miles Davis's "Kind Of Blue" and "Sketches Of Spain", John Coltrane's "Giant Steps", Tadd Dameron and John Coltrane's "Mating Call", Sonny Rollins's "Saxophone Colossus", Art Blakey's "Moanin", "Thelonious Monk Quartet With John Coltrane At Carnegie Hall" (an amazing live recording the existence of which was unknown until 3 years ago), Ornette Coleman's "The Shape Of Jazz To Come", Albert Ayler's "Spiritual Unity", and Pharoah Sanders's "Karma". That list progresses from the late 50s into the early 60s and into free jazz as it goes on, so be forewarned of that if you are one of the many who stops liking jazz when it hits the free jazz era.

good list there mate, have you heard ornette's 'On Tenor'. It's awesome, like in the literal meaning: you listen to it in awe. it's one of those albums where the more you crank it the better it sounds... and it's free as fuck!

All you need to know about the blues. Or at least that's where I'd start. Skip James has the most hair raising voice ever. You might remember him from the record they play in Ghost World. Robert Johnson is the original, sold my soul to the devil for otherworldy guitar skills, guy.

You can also explore like Son House, Muddy Watters, annnnnnnd Blind Willie McTell....also Blind Lemon Jefferson.

Jelly Roll Mourton sounds fantastic and I haven't even heard him. I remember liking the record they played in Ghost World too. Thanks for the recommendations, I love blues artists with otherwordly voices (hence my fascination with Howlin' Wolf and Satchmo).

EDIT: Skip James croons like an angel about shooting and burying his love. Wowzers.